ATE17856T1 - FURY INTERMEDIATE PRODUCTS FOR CARDENOLIDES, THEIR SYNTHESIS AND PRODUCTION OF CARDENOLIDES AND THEIR ISOMERS. - Google Patents

FURY INTERMEDIATE PRODUCTS FOR CARDENOLIDES, THEIR SYNTHESIS AND PRODUCTION OF CARDENOLIDES AND THEIR ISOMERS.

Info

Publication number
ATE17856T1
ATE17856T1 AT80303433T AT80303433T ATE17856T1 AT E17856 T1 ATE17856 T1 AT E17856T1 AT 80303433 T AT80303433 T AT 80303433T AT 80303433 T AT80303433 T AT 80303433T AT E17856 T1 ATE17856 T1 AT E17856T1
Authority
AT
Austria
Prior art keywords
cardenolides
isomers
furyl
fury
synthesis
Prior art date
Application number
AT80303433T
Other languages
German (de)
Inventor
Karel Wiesner
Thomas Y R C O University Tsai
P O Box Chemistry
Original Assignee
Advance Biofactures Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Advance Biofactures Corp filed Critical Advance Biofactures Corp
Application granted granted Critical
Publication of ATE17856T1 publication Critical patent/ATE17856T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention relates to furyl intermediates and the preparation thereof, said intermediates being particularly useful in the preparation of synthetic cardenolides and their isomers. The process provides for the reaction of an unsaturated steroidal 17 ketone with a beta -furyl compound to produce an allylic alcohol which is subjected to acetylation and allylic rearrangement. The resulting material is then hydrogenated to produce the furyl intermediate. Cardenolides are formed therefrom by oxidation of the furyl intermediates.
AT80303433T 1979-09-28 1980-09-29 FURY INTERMEDIATE PRODUCTS FOR CARDENOLIDES, THEIR SYNTHESIS AND PRODUCTION OF CARDENOLIDES AND THEIR ISOMERS. ATE17856T1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/080,004 US4259240A (en) 1979-09-28 1979-09-28 Synthesis of furyl intermediates, and cardenolides and their isomers prepared therefrom
EP80303433A EP0027023B1 (en) 1979-09-28 1980-09-29 Furyl intermediates of cardenolides, their synthesis and production of cardenolides and their isomers therefrom

Publications (1)

Publication Number Publication Date
ATE17856T1 true ATE17856T1 (en) 1986-02-15

Family

ID=22154308

Family Applications (1)

Application Number Title Priority Date Filing Date
AT80303433T ATE17856T1 (en) 1979-09-28 1980-09-29 FURY INTERMEDIATE PRODUCTS FOR CARDENOLIDES, THEIR SYNTHESIS AND PRODUCTION OF CARDENOLIDES AND THEIR ISOMERS.

Country Status (6)

Country Link
US (1) US4259240A (en)
EP (1) EP0027023B1 (en)
JP (2) JPS5657800A (en)
AT (1) ATE17856T1 (en)
CA (1) CA1159050A (en)
DE (1) DE3071409D1 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4380624A (en) * 1981-07-31 1983-04-19 Advance Biofactures Corp. Novel isomers of bufalin and resibufogenin and their preparation
CA1241324A (en) * 1984-03-08 1988-08-30 Paul A. Aristoff Interphenylene carbacyclin derivatives
GB8606105D0 (en) * 1986-03-12 1986-04-16 Glaxo Group Ltd Chemical compounds
DE4221636C1 (en) * 1992-07-01 1994-03-31 Sigma Tau Ind Farmaceuti Cyclopentane perhydrophenanthrene-17beta- (3-furyl) -3 derivatives
DE4221538C1 (en) * 1992-07-01 1994-03-31 Sigma Tau Ind Farmaceuti 14-deoxy-14alpha-cardenolide-3beta-thio derivatives
DE4221635C1 (en) * 1992-07-01 1994-05-05 Sigma Tau Ind Farmaceuti 3beta-digitoxigenin and 3beta-dihydrodigitoxigenin derivatives
NZ274694A (en) * 1993-10-27 1998-01-26 Merrell Pharma Inc Androst-16-en-3-ol derivatives having a (thi)azacycloalkyl group substituted by amino at c-17 or by unsubstituted pyrrole, thienyl or furanyl
CN102964417A (en) * 2012-11-30 2013-03-13 华中药业股份有限公司 Synthetic method of 17-hydroxy tetrahydropyran ether steroid

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3398138A (en) * 1966-05-24 1968-08-20 American Home Prod Novel cardenolides and derivatives
GB1553222A (en) * 1975-05-07 1979-09-26 Steele Chemical Co Ltd 14 - hydroxy 3- eoxycardenolides
DE2744255A1 (en) * 1976-10-05 1978-04-06 Ciba Geigy Ag PROCESS FOR PRODUCING NEW STEROID COMPOUNDS WITH 19 HOURS OF OXYGEN FUNCTION

Also Published As

Publication number Publication date
JPS5657800A (en) 1981-05-20
JPH0276897A (en) 1990-03-16
JPH0210840B2 (en) 1990-03-09
DE3071409D1 (en) 1986-03-20
CA1159050A (en) 1983-12-20
EP0027023B1 (en) 1986-02-05
US4259240A (en) 1981-03-31
EP0027023A1 (en) 1981-04-15
JPH0372240B2 (en) 1991-11-18

Similar Documents

Publication Publication Date Title
Wolfrom et al. Chemical Interactions of Amino Compounds and Sugars. III. 1 The Conversion of D-Glucose to 5-(Hydroxymethyl)-2-furaldehyde2
DE1230783B (en) Process for the preparation of polyenketones
ATE17856T1 (en) FURY INTERMEDIATE PRODUCTS FOR CARDENOLIDES, THEIR SYNTHESIS AND PRODUCTION OF CARDENOLIDES AND THEIR ISOMERS.
DE2359891A1 (en) PROCESS FOR THE PRODUCTION OF FURANONE DERIVATIVES
ES2128295T3 (en) SUBSTITUTED CYCLICAL KETONES, SUBSTITUTED CYCLICAL ENONAS AND PROCEDURE FOR THEIR PREPARATION.
ES426340A1 (en) PROCEDURE FOR OBTAINING LACTONES.
DE2151492B2 (en) METHOD FOR PREPARING P-MENTHADIEN- (1,8) -OL- (4)
DE68916634T2 (en) Alicyclic esters and their use as fragrance components.
ES358102A1 (en) Acyl-cyclododecenes,acyl-cyclododecanes and a process for producing them
EP0262388B1 (en) Derivatives of 2-tert.-butyl-4-methyl-cyclohexanol, their preparation and use as fragrance compounds
US2501199A (en) 2-p-menthyl carbinyl acetate
ES477656A1 (en) Solid modified azulmic acids with intact polycyclic structure, process for their preparation and their use.
DE2209372C2 (en) 3 Oxa bicyclo square bracket to 10 3 0 square bracket to pentadecene (6) and a method for its manufacture and its use as a fragrance
EP0026323B1 (en) 4(5)-acetyl-9,9-dimethyltricyclo-(4,4,0,1(8,10))-undec-1-ene, its preparation and use as odorant, and odorant composition containing it
EP0085937B1 (en) Perfume with a tricyclic ring structure
DE2246867A1 (en) TETRAHYDROXY-BICYCLO- SQUARE BRACKET ON 3.3.0 SQUARE BRACKET TO -OCTANE
DE68919780T2 (en) Bicyclic oxygen-containing derivatives and their use as perfuming ingredients.
CH583035A5 (en)
EP0051240B1 (en) Acetylcycloundecane and acetylcycloundecene, their application and perfumed compositions containing them
DE1264441B (en) Process for the production of 17alpha-AEthynyl-delta 5 (10-19-nor-androsten-17beta-ol-3-one and 17alpha-AEthynil-19-nor-testosterone and its esters
DE2633665C2 (en) 2,5-dimethyl-3-carbobenzyloxy-tetrahydrofuran-4-one
DE1693162C3 (en) Process for the production of epoxides and their use as fragrances
DE1593948C (en) 4 (3), 4 (3) -Dimethylperhydronaphthospiro-1,3-tetrahydrofuran and process for its preparation
EP0472123B1 (en) Propellanes
EP0051260A1 (en) Methyl-4-oxatricyclo (5.2.1.02,6)dec-8-en-3-on and methyl-4-oxatricyclo (5.2.1.02,6)decan-3-on, their preparation and their use as perfume articles

Legal Events

Date Code Title Description
UEP Publication of translation of european patent specification
REN Ceased due to non-payment of the annual fee